Nitric Acid → 6-Nitrophthalide

Participants

Reaction Steps

Three portions of a mixture of concentrated nitric acid (0.6 ml. each portion) and concentrated sulfuric acid (0.66 ml. each portion) were added to a mixture of 3-(2,4-bis(dimethylamino)phenyl)-3-(4-(dimethylamino)phenyl)phthalide (4.17 g.) and concentrated sulfuric acid (20 ml.) with cooling. After each addition the temperature was allowed to rise to room temperature. The resulting mixture was poured onto ice and the resulting mixture was basified, affording 3-(2,4-bis(dimethylamino)phenyl)-3-(4-(dimethylamino)phenyl)-5 or 6-nitrophthalide (I: X = Y4 = (CH3)2N, Y2 = Z4 = Z7 = H, Z5 or Z6 = O2N and the other of Z5 or Z6 = H) or a mixture of both.

Provenance & Evidence